US4045555A - Method for the photostabilization of polyhydroxylated sterols and stabilized biological insecticidal product obtained thereby - Google Patents
Method for the photostabilization of polyhydroxylated sterols and stabilized biological insecticidal product obtained thereby Download PDFInfo
- Publication number
- US4045555A US4045555A US05/292,295 US29229572A US4045555A US 4045555 A US4045555 A US 4045555A US 29229572 A US29229572 A US 29229572A US 4045555 A US4045555 A US 4045555A
- Authority
- US
- United States
- Prior art keywords
- hormone
- hormones
- weight
- formulation
- insect
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired - Lifetime
Links
- 229930182558 Sterol Natural products 0.000 title claims abstract description 7
- 150000003432 sterols Chemical class 0.000 title claims abstract description 7
- 235000003702 sterols Nutrition 0.000 title claims abstract description 7
- 238000000034 method Methods 0.000 title claims description 7
- 230000000749 insecticidal effect Effects 0.000 title description 5
- 230000000176 photostabilization Effects 0.000 title description 3
- 239000005556 hormone Substances 0.000 claims abstract description 41
- 229940088597 hormone Drugs 0.000 claims abstract description 41
- 230000029052 metamorphosis Effects 0.000 claims abstract description 18
- 241000238631 Hexapoda Species 0.000 claims abstract description 16
- 239000000203 mixture Substances 0.000 claims abstract description 16
- 239000000126 substance Substances 0.000 claims abstract description 12
- 238000009472 formulation Methods 0.000 claims abstract description 11
- 239000002253 acid Substances 0.000 claims abstract description 8
- 230000005855 radiation Effects 0.000 claims abstract description 6
- 150000003839 salts Chemical class 0.000 claims abstract description 6
- 150000007513 acids Chemical class 0.000 claims abstract description 5
- 150000001565 benzotriazoles Chemical class 0.000 claims abstract description 5
- 239000002917 insecticide Substances 0.000 claims description 6
- 230000003711 photoprotective effect Effects 0.000 claims description 6
- 150000001875 compounds Chemical class 0.000 claims description 5
- 230000000087 stabilizing effect Effects 0.000 claims description 5
- 230000001066 destructive effect Effects 0.000 claims description 4
- 230000003472 neutralizing effect Effects 0.000 claims description 3
- 150000002576 ketones Chemical class 0.000 claims description 2
- 238000004519 manufacturing process Methods 0.000 claims 1
- 239000000243 solution Substances 0.000 description 19
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 9
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
- 239000003381 stabilizer Substances 0.000 description 9
- 238000002360 preparation method Methods 0.000 description 7
- 239000002904 solvent Substances 0.000 description 7
- LRJUYAVTHIEHAI-LHBNDURVSA-N Muristerone Chemical compound C1[C@@H](O)[C@@H](O)C[C@]2(C)[C@@H]([C@H](O)C[C@@]3([C@@H]([C@@](C)(O)[C@H](O)CCC(C)C)CC[C@]33O)C)C3=CC(=O)[C@@]21O LRJUYAVTHIEHAI-LHBNDURVSA-N 0.000 description 6
- WSSJONWNBBTCMG-UHFFFAOYSA-N 2-hydroxybenzoic acid (3,3,5-trimethylcyclohexyl) ester Chemical compound C1C(C)(C)CC(C)CC1OC(=O)C1=CC=CC=C1O WSSJONWNBBTCMG-UHFFFAOYSA-N 0.000 description 5
- UWSMKYBKUPAEJQ-UHFFFAOYSA-N 5-Chloro-2-(3,5-di-tert-butyl-2-hydroxyphenyl)-2H-benzotriazole Chemical compound CC(C)(C)C1=CC(C(C)(C)C)=CC(N2N=C3C=C(Cl)C=CC3=N2)=C1O UWSMKYBKUPAEJQ-UHFFFAOYSA-N 0.000 description 5
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 5
- YXPVYQIMXPYFSF-UHFFFAOYSA-N Makisterone A Natural products CC(C)C(C)(O)CC(O)C(C)(O)C1CCC2(O)C3=CC(=O)C4CC(O)C(O)CC4(C)C3CCC12C YXPVYQIMXPYFSF-UHFFFAOYSA-N 0.000 description 5
- IJRBORPEVKCEQD-JMQWOFAPSA-N Makisterone A Chemical compound C1[C@@H](O)[C@@H](O)C[C@]2(C)[C@@H](CC[C@@]3([C@@H]([C@@](C)(O)[C@H](O)C[C@@H](C)C(C)(C)O)CC[C@]33O)C)C3=CC(=O)[C@@H]21 IJRBORPEVKCEQD-JMQWOFAPSA-N 0.000 description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- DNIAPMSPPWPWGF-GSVOUGTGSA-N (R)-(-)-Propylene glycol Chemical compound C[C@@H](O)CO DNIAPMSPPWPWGF-GSVOUGTGSA-N 0.000 description 3
- FJGQBLRYBUAASW-UHFFFAOYSA-N 2-(benzotriazol-2-yl)phenol Chemical class OC1=CC=CC=C1N1N=C2C=CC=CC2=N1 FJGQBLRYBUAASW-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- DNIAPMSPPWPWGF-UHFFFAOYSA-N monopropylene glycol Natural products CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
- 239000000843 powder Substances 0.000 description 3
- 235000013772 propylene glycol Nutrition 0.000 description 3
- ZMWRRFHBXARRRT-UHFFFAOYSA-N 2-(benzotriazol-2-yl)-4,6-bis(2-methylbutan-2-yl)phenol Chemical compound CCC(C)(C)C1=CC(C(C)(C)CC)=CC(N2N=C3C=CC=CC3=N2)=C1O ZMWRRFHBXARRRT-UHFFFAOYSA-N 0.000 description 2
- 230000031018 biological processes and functions Effects 0.000 description 2
- 230000015556 catabolic process Effects 0.000 description 2
- 238000006731 degradation reaction Methods 0.000 description 2
- -1 ecdisone Chemical compound 0.000 description 2
- 235000019441 ethanol Nutrition 0.000 description 2
- 230000004224 protection Effects 0.000 description 2
- 230000001681 protective effect Effects 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 230000006641 stabilisation Effects 0.000 description 2
- 238000011105 stabilization Methods 0.000 description 2
- 239000000725 suspension Substances 0.000 description 2
- HJIAMFHSAAEUKR-UHFFFAOYSA-N (2-hydroxyphenyl)-phenylmethanone Chemical class OC1=CC=CC=C1C(=O)C1=CC=CC=C1 HJIAMFHSAAEUKR-UHFFFAOYSA-N 0.000 description 1
- NKDFYOWSKOHCCO-YPVLXUMRSA-N 20-hydroxyecdysone Chemical compound C1[C@@H](O)[C@@H](O)C[C@]2(C)[C@@H](CC[C@@]3([C@@H]([C@@](C)(O)[C@H](O)CCC(C)(O)C)CC[C@]33O)C)C3=CC(=O)[C@@H]21 NKDFYOWSKOHCCO-YPVLXUMRSA-N 0.000 description 1
- DKPFZGUDAPQIHT-UHFFFAOYSA-N Butyl acetate Natural products CCCCOC(C)=O DKPFZGUDAPQIHT-UHFFFAOYSA-N 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- 230000002745 absorbent Effects 0.000 description 1
- 239000002250 absorbent Substances 0.000 description 1
- 230000001476 alcoholic effect Effects 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- QRUDEWIWKLJBPS-UHFFFAOYSA-N benzotriazole Chemical class C1=CC=C2N[N][N]C2=C1 QRUDEWIWKLJBPS-UHFFFAOYSA-N 0.000 description 1
- 239000012964 benzotriazole Substances 0.000 description 1
- 238000013375 chromatographic separation Methods 0.000 description 1
- 239000012141 concentrate Substances 0.000 description 1
- 239000000470 constituent Substances 0.000 description 1
- 230000006378 damage Effects 0.000 description 1
- FPAFDBFIGPHWGO-UHFFFAOYSA-N dioxosilane;oxomagnesium;hydrate Chemical compound O.[Mg]=O.[Mg]=O.[Mg]=O.O=[Si]=O.O=[Si]=O.O=[Si]=O.O=[Si]=O FPAFDBFIGPHWGO-UHFFFAOYSA-N 0.000 description 1
- 230000008034 disappearance Effects 0.000 description 1
- 239000003480 eluent Substances 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- FUZZWVXGSFPDMH-UHFFFAOYSA-N hexanoic acid Chemical compound CCCCCC(O)=O FUZZWVXGSFPDMH-UHFFFAOYSA-N 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 230000001473 noxious effect Effects 0.000 description 1
- 239000000546 pharmaceutical excipient Substances 0.000 description 1
- 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 229920003023 plastic Polymers 0.000 description 1
- 229920001223 polyethylene glycol Polymers 0.000 description 1
- 230000002035 prolonged effect Effects 0.000 description 1
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 1
- 239000003223 protective agent Substances 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- 235000015112 vegetable and seed oil Nutrition 0.000 description 1
- 239000008158 vegetable oil Substances 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
Classifications
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N25/00—Biocides, pest repellants or attractants, or plant growth regulators, characterised by their forms, or by their non-active ingredients or by their methods of application, e.g. seed treatment or sequential application; Substances for reducing the noxious effect of the active ingredients to organisms other than pests
- A01N25/22—Biocides, pest repellants or attractants, or plant growth regulators, characterised by their forms, or by their non-active ingredients or by their methods of application, e.g. seed treatment or sequential application; Substances for reducing the noxious effect of the active ingredients to organisms other than pests containing ingredients stabilising the active ingredients
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07J—STEROIDS
- C07J31/00—Normal steroids containing one or more sulfur atoms not belonging to a hetero ring
- C07J31/006—Normal steroids containing one or more sulfur atoms not belonging to a hetero ring not covered by C07J31/003
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N63/00—Biocides, pest repellants or attractants, or plant growth regulators containing microorganisms, viruses, microbial fungi, animals or substances produced by, or obtained from, microorganisms, viruses, microbial fungi or animals, e.g. enzymes or fermentates
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10S424/00—Drug, bio-affecting and body treating compositions
- Y10S424/12—Fertilization attaching inhibition
Definitions
- This invention relates to the photostabilization of hormones of the metamorphosis of insects, which can be used as biological insecticides.
- the stabilization process according to the present invention is characterized thus in that ecdisterols, which are useful as biological-action insecticides, are admixed with stabilizing amounts of absorbent and photoprotective substances. More particularly, the objects of the present invention are attained when the compounds which absorb the ultraviolet radiations are selected from among those which are conventionally used for protecting plastics materials, such as o-hydroxybenzophenones, benzotriazoles and substituted phenylglioxylic acids and their salts. Most advantageous results are obtained when the stabilizer is selected from the last two classes of compounds.
- the biological insecticidal product according to the present invention is characterized in that it contains, as the active principle, one or more hormones of insect metamorphosis and, as the stabilizer, a photoprotective substance which is capable of neutralizing the destructive effects of ultraviolet radiations.
- concentrations which are recommendable for these substances having a protective action against ultraviolet rays in order that a stabilizing effect may be obtained and thus the protection of the insect metamorphosis hormones, vary according to the characteristics of the formulation and are comprised between 0.005 and 5 grams per 100 parts by weight of the final formulate. In general, concentrations ranging from the lower limiting value indicated above to a weight equal to that of the hormones, which are present in the formulation, are sufficient.
- the stabilizing effects of the photoprotective and UV-ray absorbing substances indicated above are displayed for dosages such as suggested in the foregoing and for a period of time which is sufficient to ensure the biological action of the metamorphosis hormones.
- Another aspect which is very important from the point of view of the application as biological insecticides of the insect metamorphosis hormones lies in that, by varying the amount of photostabilizing substances present in the formulation, it is possible to govern as desired the useful life or duration of the stability period of the insecticidal product, before the latter undergoes the photochemical action and the insecticidal action may disappear.
- the metamorphosis hormones which among others are sensitive to stabilization, are for example: ecdisone, crustecdisone, (ecdisterone or ecdisone beta), makisterone A, muristerone.
- ecdisone crustecdisone
- ecdisterone or ecdisone beta makisterone A
- muristerone a total extract containing ecdisterols and the substances indicated above is appropriately stabilized for use.
- Such an extract is obtained according to the teachings of the aforementioned patent application.
- the photostabilizers should be intimately admixed with the active principle (s) and the other constituents of the formulation if said powdered preparations are intended.
- the stabilizer as dissolved in appropriate solvent in the form of a master solution, is added to the solution, or suspension as the case may be, of the hormone (s) of the metamorphosis and the other components.
- solvents which are adapted to the preparation of the master solutions of photostabilizers belonging to the class of benzotriazoles one can use, for example: acetone, ethyl acetate, butyl acetate, benzene, toluene, ethanol, methanol, ligroin.
- phenylglioxylic acid and its salts In the case of derivatives of phenylglioxylic acid and its salts, one can employ, instead, for the preparation of the master solutions, glycerol, 1,2-propanediol, nor. propanol, polyethylene glycols and vegetable oils. Lastly, aqueous master solutions can be prepared for phenylglioxylic acid salts.
- the stabilized solutions of metamorphosis hormones can also be prepared by concurrently dissolving in one of the above indicated solvents, or in admixtures of the above indicated solvents, the photostabilizer and the hormone (s); subsequently this solution can be dispersed in the excipient or the solid components of the formulation and then the solvent(s) are evaporated by mere exposure to air or by keeping the mass under vacuum.
- the dried residue can then be finely ground and the powder used as such, or the residue can be taken up, in turn, with appropriate solvents in order to obtain a concentrate.
- the stabilized preparations of insect metamorphosis hormones as obtained after the criteria indicated above and as more detailedly disclosed in the following examples can be used either directly as insecticides or they can be introduced in more complex formulations.
- crustecdisone ecdisterone, beta ecdisone
- an alkylated 2-(2-hydroxyphenyl)-2H-benzotriazole such as Tinuvin 327
- the two products should have been previously ground to a mesh size of 60 mesh/centimeter.
- the powder is shaken in a powder mixture until obtaining a homogenous admixture of the two substances.
- the thusly obtained composition is a stabilized crustecdisone composition.
- Example 2 The procedure is similar to that of Example 1, by employing instead of crustecdisone the same amount of an extract which contains crustecdisone, makisterone A, ecdisone, muristerone and other polyhydroxylated sterols.
- acetone there are dissolved 1 gram of ecdisone and 100 milligrams of an alkylated 2-(2-hydroxyphenyl)-2H-benzotriazole (such as Tinuvin 328).
- the solution in acetone is spread, in a mixer, over one kilogram of airclassified talc powder.
- Acetone is removed from the mass by keeping it in a desiccator under vacuum heated at 40° C. until completely evaporating of the solvent.
- a stabilized crustecdisone preparation is thus obtained.
- crustecdisone 0.5 grams are weighed and dissolved at 50° C. in 200 mls of 1,2-propanediol. There are weighed 25 milligrams of an alkyl substituted 2-(2-hydroxyphenyl)-2H-benzotriazole (such as Tinuvin 327) and are dissolved in 175 mls of 1,2-propanediol. This second solution is combined with the first one and then water is added to make up to 500 mls. The thusly obtained solution is a stabilized crustecdisone solution.
- a stabilized ecdisterone aqueous solution is thus obtained.
- Example 7 The procedure is similar to that of Example 7 using in lieu of ecdisterone, 2 grams of an extract made of crustecdisone, makisterone A, ecdisone, muristerone and other polyhydroxylated sterols.
- Each test is the average of five readings.
- the quantitative determination of the hormone is carried out by chromatographic separation on a thin layer using as the eluent system a mixture of methylene chloride:methanol:water in the ratios 79:15:1 on prepared Merck Kieselgel F 254 art. 5715 plates. The spots are then quantitatively evaluated with a Vitatron densometer. All the tests are referred to measurements taken after exposure to the light of a Philips HPK 125 lamp during a period of one hour and a half.
- the time of 1.5 hours has been selected on the basis of the fact that this is the time required for the total destruction of the hormone which is present in the non-protected solution exposed to the lamp light.
Landscapes
- Life Sciences & Earth Sciences (AREA)
- Health & Medical Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Zoology (AREA)
- Engineering & Computer Science (AREA)
- Pest Control & Pesticides (AREA)
- Dentistry (AREA)
- Wood Science & Technology (AREA)
- Plant Pathology (AREA)
- Environmental Sciences (AREA)
- Agronomy & Crop Science (AREA)
- Biotechnology (AREA)
- Microbiology (AREA)
- Virology (AREA)
- Toxicology (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Steroid Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| IT29276/71 | 1971-09-29 | ||
| IT29276/71A IT945969B (it) | 1971-09-29 | 1971-09-29 | Procedimento per la stabilizzazio ne di steroli poliidrossilati e prodotto insetticida biologico sta bilizzato cosi ottenuto |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| US4045555A true US4045555A (en) | 1977-08-30 |
Family
ID=11226666
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US05/292,295 Expired - Lifetime US4045555A (en) | 1971-09-29 | 1972-09-26 | Method for the photostabilization of polyhydroxylated sterols and stabilized biological insecticidal product obtained thereby |
Country Status (15)
| Country | Link |
|---|---|
| US (1) | US4045555A (es) |
| JP (1) | JPS4840928A (es) |
| AU (1) | AU467967B2 (es) |
| BR (1) | BR7206805D0 (es) |
| CA (1) | CA966776A (es) |
| DD (1) | DD101547A1 (es) |
| DE (1) | DE2247507C2 (es) |
| ES (1) | ES407144A1 (es) |
| FR (1) | FR2154656B1 (es) |
| GB (1) | GB1401645A (es) |
| IT (1) | IT945969B (es) |
| NL (1) | NL7213159A (es) |
| OA (1) | OA04185A (es) |
| SE (1) | SE7212543L (es) |
| ZA (1) | ZA726611B (es) |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4552885A (en) * | 1981-12-24 | 1985-11-12 | Ciba Geigy Corporation | Stabilized fungicide compositions |
| US4622315A (en) * | 1983-02-10 | 1986-11-11 | The Regents Of The University Of California | Additives for improved pesticide photstability |
| CN118077701A (zh) * | 2022-11-25 | 2024-05-28 | 沈阳中化农药化工研发有限公司 | 一种杀虫和杀螨制剂及其应用 |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS57175109A (en) * | 1981-04-21 | 1982-10-28 | Hokko Chem Ind Co Ltd | Improved purified machine oil emulsion |
| JPS60182659A (ja) * | 1984-02-29 | 1985-09-18 | Shin Kobe Electric Mach Co Ltd | 極板自動練塗装置 |
| JPH05121068A (ja) * | 1991-10-29 | 1993-05-18 | Shin Kobe Electric Mach Co Ltd | 極板製造用自動ペースト充填装置及びその制御方法 |
Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3189615A (en) * | 1956-12-14 | 1965-06-15 | Geigy Ag J R | 2-aryl-4, 5-arylo-1, 2, 3-triazole |
| US3453362A (en) * | 1966-05-10 | 1969-07-01 | Fmc Corp | Insect control methods and compositions |
| GB1159137A (en) | 1966-01-19 | 1969-07-23 | Int Minerals & Chem Corp | Stabilized Microbial Insecticides |
-
1971
- 1971-09-29 IT IT29276/71A patent/IT945969B/it active
-
1972
- 1972-09-26 CA CA152,553A patent/CA966776A/en not_active Expired
- 1972-09-26 US US05/292,295 patent/US4045555A/en not_active Expired - Lifetime
- 1972-09-27 AU AU47159/72A patent/AU467967B2/en not_active Expired
- 1972-09-27 ZA ZA726611A patent/ZA726611B/xx unknown
- 1972-09-27 FR FR7234224A patent/FR2154656B1/fr not_active Expired
- 1972-09-27 GB GB4467872A patent/GB1401645A/en not_active Expired
- 1972-09-28 OA OA54703A patent/OA04185A/xx unknown
- 1972-09-28 NL NL7213159A patent/NL7213159A/xx not_active Application Discontinuation
- 1972-09-28 SE SE7212543A patent/SE7212543L/xx unknown
- 1972-09-28 DE DE2247507A patent/DE2247507C2/de not_active Expired
- 1972-09-28 DD DD165924A patent/DD101547A1/xx unknown
- 1972-09-29 JP JP47097254A patent/JPS4840928A/ja active Pending
- 1972-09-29 ES ES407144A patent/ES407144A1/es not_active Expired
- 1972-09-29 BR BR6805/72A patent/BR7206805D0/pt unknown
Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3189615A (en) * | 1956-12-14 | 1965-06-15 | Geigy Ag J R | 2-aryl-4, 5-arylo-1, 2, 3-triazole |
| GB1159137A (en) | 1966-01-19 | 1969-07-23 | Int Minerals & Chem Corp | Stabilized Microbial Insecticides |
| US3453362A (en) * | 1966-05-10 | 1969-07-01 | Fmc Corp | Insect control methods and compositions |
Non-Patent Citations (1)
| Title |
|---|
| Chemical Abstracts, vol. 64 (1966), p. 14642b. * |
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4552885A (en) * | 1981-12-24 | 1985-11-12 | Ciba Geigy Corporation | Stabilized fungicide compositions |
| US4622315A (en) * | 1983-02-10 | 1986-11-11 | The Regents Of The University Of California | Additives for improved pesticide photstability |
| CN118077701A (zh) * | 2022-11-25 | 2024-05-28 | 沈阳中化农药化工研发有限公司 | 一种杀虫和杀螨制剂及其应用 |
| CN118077701B (zh) * | 2022-11-25 | 2025-07-18 | 沈阳中化农药化工研发有限公司 | 一种杀虫和杀螨制剂及其应用 |
Also Published As
| Publication number | Publication date |
|---|---|
| GB1401645A (en) | 1975-07-16 |
| DE2247507C2 (de) | 1982-04-29 |
| IT945969B (it) | 1973-05-10 |
| ES407144A1 (es) | 1975-11-01 |
| SE7212543L (es) | 1973-03-30 |
| NL7213159A (es) | 1973-04-02 |
| DE2247507A1 (de) | 1973-04-05 |
| AU4715972A (en) | 1974-04-04 |
| FR2154656B1 (es) | 1976-05-21 |
| DD101547A1 (es) | 1973-11-12 |
| ZA726611B (en) | 1973-07-25 |
| BR7206805D0 (pt) | 1973-09-18 |
| AU467967B2 (en) | 1975-12-18 |
| CA966776A (en) | 1975-04-29 |
| OA04185A (fr) | 1979-12-31 |
| JPS4840928A (es) | 1973-06-15 |
| FR2154656A1 (es) | 1973-05-11 |
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